CN106423280A - Preparation of cationic organic polymer and method for catalyzing fixation of carbon dioxide - Google Patents
Preparation of cationic organic polymer and method for catalyzing fixation of carbon dioxide Download PDFInfo
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- CN106423280A CN106423280A CN201610827635.8A CN201610827635A CN106423280A CN 106423280 A CN106423280 A CN 106423280A CN 201610827635 A CN201610827635 A CN 201610827635A CN 106423280 A CN106423280 A CN 106423280A
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- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 229910002092 carbon dioxide Inorganic materials 0.000 title claims abstract description 14
- 239000001569 carbon dioxide Substances 0.000 title claims abstract description 14
- 229920000620 organic polymer Polymers 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 125000002091 cationic group Chemical group 0.000 title abstract description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 32
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 150000005676 cyclic carbonates Chemical class 0.000 claims abstract description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 3
- -1 olefin epoxide Chemical class 0.000 claims abstract description 3
- 238000001291 vacuum drying Methods 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 6
- 150000002460 imidazoles Chemical class 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 5
- 238000004440 column chromatography Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- 238000005119 centrifugation Methods 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 4
- VEUMANXWQDHAJV-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol Chemical compound OC1=CC=CC=C1C=NCCN=CC1=CC=CC=C1O VEUMANXWQDHAJV-UHFFFAOYSA-N 0.000 claims description 3
- 238000000605 extraction Methods 0.000 claims description 3
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 3
- 241000790917 Dioxys <bee> Species 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 4
- 239000002585 base Substances 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 2
- 239000000178 monomer Substances 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 abstract description 5
- 238000005859 coupling reaction Methods 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 230000001588 bifunctional effect Effects 0.000 abstract 2
- XCGAYRKEBXJPJG-UHFFFAOYSA-N 2,4,6-tri(imidazol-1-yl)-1,3,5-triazine Chemical compound C1=NC=CN1C1=NC(N2C=NC=C2)=NC(N2C=NC=C2)=N1 XCGAYRKEBXJPJG-UHFFFAOYSA-N 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 238000006735 epoxidation reaction Methods 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000009429 distress Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- PLHJDBGFXBMTGZ-WEVVVXLNSA-N furazolidone Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)OCC1 PLHJDBGFXBMTGZ-WEVVVXLNSA-N 0.000 description 1
- 229960001625 furazolidone Drugs 0.000 description 1
- 238000006206 glycosylation reaction Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/1691—Coordination polymers, e.g. metal-organic frameworks [MOF]
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
- B01J31/181—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine
- B01J31/1815—Cyclic ligands, including e.g. non-condensed polycyclic ligands, comprising at least one complexing nitrogen atom as ring member, e.g. pyridine with more than one complexing nitrogen atom, e.g. bipyridyl, 2-aminopyridine
-
- B01J35/60—
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
- B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
- B01J2531/0241—Rigid ligands, e.g. extended sp2-carbon frameworks or geminal di- or trisubstitution
- B01J2531/0252—Salen ligands or analogues, e.g. derived from ethylenediamine and salicylaldehyde
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/30—Complexes comprising metals of Group III (IIIA or IIIB) as the central metal
- B01J2531/31—Aluminium
Abstract
The invention relates to preparation of a bifunctional cationic porous organic polymer on the basis of Salen-Al and a method for catalyzing fixation of carbon dioxide into cyclic carbonate. The bifunctional cationic porous organic polymer catalyst is prepared from a Salen-Al ligand and 2,4,6-tris(imidazole-1-yl)-1,3,5 triazine through a coupling reaction. The catalyst is simple to prepare and has higher activity and selectivity for catalysis of the reaction of carbon dioxide and olefin epoxide, and the catalyst is separated from a product easily and can be recycled several times.
Description
Technical field
The invention belongs to carbon dioxide fixation catalyst technical field and in particular to one kind synthesized by Salen-Al difunctional
The preparation method of cation porous organic polymer catalyst Al-CPOP, and catalysis carbon dioxide fixation position cyclic carbonate is anti-
The application answered.
Background technology
Cyclic carbonate is a kind of very important synthetic intermediate, the organic solvent of function admirable, can dissolve multiple poly-
Compound；Separately can be used as organic intermediate, alternative oxirane is used for dioxy glycosylation reaction, and is carbonate production by transesterification two
The primary raw material of methyl esters；Also act as the synthesis raw material of furazolidone, waterglass system slurry, fibre trimmer etc.；Additionally, also should
For in lithium battery electrolytes.But during traditional cyclic carbonate produces, multiple accessory substances can be produced, simultaneously tradition
Homogeneous catalyst separation in distress, the shortcomings of easily decompose and cannot recycle, can greatly increase the difficulty of product postprocessing
With time fund input.Therefore people's effort is realized homogeneous catalyst out-phase by the fixation of catalyst and is solved above asking
Topic.At present, usually Salen class catalyst is loaded to the silicon class inorganic material such as molecular sieve or Salen-Al made part
It is prepared into metal organic frame (MOF).But in this two classes method, the former needs a large amount of carriers, and load capacity is not high, and cycle performance is not
Good, the latter is due to being the framework that coordination is formed, and the solvent molecule inside MOF once loses and is likely to cause framework and collapses
Collapse, thus unstable.And porous organic polymer is readily synthesized due to it, there is big specific surface area, in the fields such as catalysis tool
There is potential using value, become the focus of Recent study.
Content of the invention
The purpose of the present invention is to propose to a kind of difunctional cation porous organic polymer prepared by coupling reaction urging
Agent and its application.
Difunctional cation porous organic polymer method for preparing catalyst proposed by the present invention, its preparation process is as follows：
Add Salen-Al part and 2,4,6- tri- (imidazoles -1- base) -1 equipped with the three-neck flask of serpentine condenser,
3,5- triazines, in the whole nitrogen atmosphere of reaction, with DMF and ethanol as solvent, 110 DEG C of back flow reaction 48 are little
When.After the completion of reaction, centrifugation, vacuum drying chamber is dried, methyl alcohol surname extraction 24 hours, and vacuum drying chamber is dried, and obtains double work(
Can cation porous organic polymer catalyst Al-CPOP.
Al-CPOP catalyst carbon dioxide fixation proposed by the present invention is that cyclic carbonate reactions steps are as follows：To
It is separately added into olefin epoxide and catalyst Al-CPOP, (wherein Al-CPOP is with poly- for the amount of both materials in reaction system
The content of the metal in compound as material amount calculate standard) ratio be 1:0.01, pressure carbon dioxide is maintained 0.1MPa,
120 DEG C of reaction temperature, after reacting 24 hours, centrifugation, catalyst is washed with acetone, dries 12 hours in vacuum drying chamber, circulation
Use；Liquid phase part anhydrous sodium sulfate drying, column chromatography for separation obtains corresponding product circular carbonic ester.
Brief description
Fig. 1 is gained catalyst transmission electron microscope picture.
Fig. 2 is gained catalyst scanning electron microscope (SEM) photograph.
Fig. 3 is the structure chart of gained catalyst.
Specific embodiment
Embodiment 1：Al-CPOP catalyst
Add Salen-Al part and 2,4,6- tri- (imidazoles -1- base) -1 equipped with the three-neck flask of serpentine condenser,
3,5- triazines, in the whole nitrogen atmosphere of reaction, with DMF and ethanol as solvent, 110 DEG C of back flow reaction 48 are little
When.After the completion of reaction, centrifugation, vacuum drying chamber is dried, methyl alcohol surname extraction 24 hours, and vacuum drying chamber is dried, and obtains double work(
Can cation porous organic polymer catalyst Al-CPOP.
Embodiment 2：Al-CPOP catalyst carbon dioxide fixation reacts for cyclic carbonate
It is separately added into epoxychloropropane and catalyst Al-CPOP, amount (the wherein Al- of both materials in reaction system
CPOP using the content of the metal in polymer as the amount of material calculate standard) ratio be 1:0.01, pressure carbon dioxide maintains
For 0.1MPa, 120 DEG C of reaction temperature, after reacting 24 hours, it is centrifuged, catalyst is washed with acetone, in vacuum drying chamber, dries 12
Hour, recycle；Liquid phase part anhydrous sodium sulfate drying, column chromatography for separation obtains corresponding product circular carbonic ester.
Embodiment 3：Al-CPOP catalyst carbon dioxide fixation reacts for cyclic carbonate
It is separately added into expoxy propane and catalyst Al-CPOP, amount (the wherein Al- of both materials in reaction system
CPOP using the content of the metal in polymer as the amount of material calculate standard) ratio be 1:0.01, pressure carbon dioxide maintains
For 0.1MPa, 120 DEG C of reaction temperature, after reacting 24 hours, it is centrifuged, catalyst is washed with acetone, in vacuum drying chamber, dries 12
Hour, recycle；Liquid phase part anhydrous sodium sulfate drying, column chromatography for separation obtains corresponding epoxidation reaction of olefines and produces
Thing.
Embodiment 4：Al-CPOP catalyst epoxidation reaction of olefines
It is separately added into epoxy styrene and catalyst Al-CPOP, amount (the wherein Al- of both materials in reaction system
CPOP using the content of the metal in polymer as the amount of material calculate standard) ratio be 1:0.01, pressure carbon dioxide maintains
For 0.1MPa, 120 DEG C of reaction temperature, after reacting 24 hours, it is centrifuged, catalyst is washed with acetone, in vacuum drying chamber, dries 12
Hour, recycle；Liquid phase part anhydrous sodium sulfate drying, column chromatography for separation obtains corresponding epoxidation reaction of olefines and produces
Thing.
The catalysis activity to multiple substrates for the table 1Al-CPOP
Claims (5)
1. a kind of difunctional cation porous organic polymer class catalyst, is named as Al-CPOP, with Salen-Al part and 2,
4,6- tri- (imidazoles -1- base) -1,3,5- triazine is coupled and obtains based on double catalytic active center Salen-Al and imidazole salts
Polymerization species catalyst.
2. a kind of preparation method of catalyst as claimed in claim 1, comprises the following steps：
(1) Salen monomer and crystal aluminum chloride be according to a certain amount of and ratio, with ethanol and chloroform as solvent, in 80 DEG C of blanket of nitrogen
Enclose middle back flow reaction one day, wash thereafter and 70 DEG C of bakings obtain Salen-Al part in 24 hours in vacuum drying chamber；
(2) Salen-Al part and 2,4,6- tri- (imidazoles -1- base) -1,3,5-triazines in nitrogen atmosphere, with N, N- dimethyl
Formamide and ethanol are solvent, and 110 DEG C are reacted 48 hours, centrifugation, and vacuum drying chamber is dried, with methyl alcohol surname extraction 24 hours,
Vacuum drying chamber is dried, and obtains Al-CPOP.
3. method as claimed in claim 2 it is characterised in that：In described step (1), Salen monomer and crystal aluminum chloride are used
Amount ratio is 1:1.2, etoh solvent and chloroform ratio are 1:1.
4. method as claimed in claim 2 it is characterised in that：In described step (2), Salen-Al part and 2,4,6- tri-
(imidazoles -1- base) -1,3,5- triazine amount ratio is 1:1.2, solvent DMF and ethanol consumption are than for 1:1.
5. a kind of catalyst carbon dioxide fixation as claimed in claim 1 is the application in cyclic carbonate reaction, its
It is characterised by comprising the following steps that：It is separately added into olefin epoxide and catalyst Al-CPOP, both things in reaction system
The ratio of the amount of matter is 1:0.01, wherein Al-CPOP calculate standard using the content of the metal in polymer as the amount of material；Dioxy
The pressure changing carbon maintains 0.1MPa, 120 DEG C of reaction temperature, after reacting 24 hours, is centrifuged, catalyst is washed with acetone, vacuum is done
Dry 12 hours in dry case, recycle；Liquid phase part anhydrous sodium sulfate drying, column chromatography for separation is reacted product accordingly
Thing cyclic carbonate.
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| CN201610827635.8A CN106423280A (en) | 2016-09-18 | 2016-09-18 | Preparation of cationic organic polymer and method for catalyzing fixation of carbon dioxide |
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| CN201610827635.8A CN106423280A (en) | 2016-09-18 | 2016-09-18 | Preparation of cationic organic polymer and method for catalyzing fixation of carbon dioxide |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107930606A (en) * | 2017-11-17 | 2018-04-20 | 中南大学 | One kind is containing triazine ring and azo bond functional group porous polymer sorbing material, porous polymer catalysis material and preparation and application |
| CN111286025A (en) * | 2020-02-18 | 2020-06-16 | 辽宁大学 | Bifunctional cationic polymer based on Salen ligand and application of bifunctional cationic polymer in catalytic preparation of cyclic carbonate |
| CN112480132A (en) * | 2020-12-02 | 2021-03-12 | 哈尔滨理工大学 | Preparation and application of covalent organic framework material based on Salen structure |
| CN113117745A (en) * | 2021-04-13 | 2021-07-16 | 昆明理工大学 | Preparation method and application of metal-free catalyst |
| CN114989408A (en) * | 2022-07-12 | 2022-09-02 | 郑州大学 | Solid-phase catalyst for carbon dioxide/epoxy compound copolymerization and preparation method thereof |
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| CN104974128A (en) * | 2015-07-24 | 2015-10-14 | 大连理工大学 | Method for preparing cyclic carbonate by using supported quaternary phosphonium salt catalyst |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107930606A (en) * | 2017-11-17 | 2018-04-20 | 中南大学 | One kind is containing triazine ring and azo bond functional group porous polymer sorbing material, porous polymer catalysis material and preparation and application |
| CN111286025A (en) * | 2020-02-18 | 2020-06-16 | 辽宁大学 | Bifunctional cationic polymer based on Salen ligand and application of bifunctional cationic polymer in catalytic preparation of cyclic carbonate |
| CN112480132A (en) * | 2020-12-02 | 2021-03-12 | 哈尔滨理工大学 | Preparation and application of covalent organic framework material based on Salen structure |
| CN113117745A (en) * | 2021-04-13 | 2021-07-16 | 昆明理工大学 | Preparation method and application of metal-free catalyst |
| CN113117745B (en) * | 2021-04-13 | 2022-05-27 | 昆明理工大学 | Preparation method and application of metal-free catalyst |
| CN114989408A (en) * | 2022-07-12 | 2022-09-02 | 郑州大学 | Solid-phase catalyst for carbon dioxide/epoxy compound copolymerization and preparation method thereof |
| CN114989408B (en) * | 2022-07-12 | 2023-04-25 | 郑州大学 | Solid phase catalyst for carbon dioxide/epoxy compound copolymerization and preparation method thereof |
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